How to Get a Private Cocktail Tasting at Brooklyn’s Most Exclusive Bar

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With only two seats and no exterior signage, the by-reservation-only Threesome Tollbooth is the coolest borough’s secret new spot for custom cocktails.

ByAvery Stone on November 10, 2017

New York is a city that revels in its small, secret spaces. In the 2000s, now-famous speakeasies like PDT and Death & Co. gained a widespread following—for their fine cocktails, yes, but also because they provided an exclusive respite from the city’s bustle. Judging by its premise alone, the Threesome Tollbooth, a reservation-only cocktail bar in Brooklyn’s East Williamsburg neighborhood, just sounds like another of these places: it is located in a supply closet of a now-shuttered restaurant that held onto its liquor license, and is just large enough to fit two guests and a bartender.

But in reality, the Tollbooth doesn’t just feel like a hideaway from the world. It feels like a world in itself.

The bar’s name, an apparent nod to the children’s fantasy novel The Phantom Tollbooth, would suggest this: in the book, a boy named Milo drives a toy car through a mysterious tollbooth and finds himself in a magical new world. The journey to the Threesome Tollbooth is equally fanciful.

Though the Tollbooth’s exact address is a secret—a friend and I received ours via email the morning of our reservation—its entrance is a graffiti-covered metal door on a quiet, factory-lined street. Once there, guests are instructed to text their bartender, one of the Tollbooth’s two co-founders: artist and architect N.D. Austin (who also helmed the Night Heron, a pop-up speakeasy in a Chelsea water tower) and lexicographer Jesse Sheidlower.

On this particular Friday evening, Sheidlower appears. He wears a salmon-colored dress shirt, a bow tie, Converse sneakers, and rimless eyeglasses. His fingernails are painted with black nail polish that has chipped slightly. His hair is dyed lavender, and frames his thin, pale face in an angled cut that falls just above his chin. At his instruction, we move through a courtyard, the restaurant’s empty interior, a side hallway, a supply closet, and then, finally, through a door within the closet, into the Tollbooth.

Peering inside, the space—featuring a brown leather banquette, a back-lit stained-glass window on the ceiling, and dark wood shelving built by Austin himself—looks impossibly small. But once Sheidlower shuts the door and folds a countertop down from the wall (which serves as both bar and buffer), the room seems to expand by the second. (The Tollbooth’s music also helps to transport: it is exclusively American singer-songwriter Tom Waits, played from a speaker fashioned out of a vintage brass instrument and an old shoe.) Then, after a sensory ritual that Sheidlower requests be kept mum (clue: it engages the ears), he selects from an elegant arsenal of tools hanging on the back of the door, and mixes our first cocktail.

Tod Seelie

The Tollbooth has no set menu, but over each approximately hour-long visit, guests are served five or six mini-cocktails that tend to progress from lighter to heavier in nature. This evening, our first is the “Gin and It,” comprised of gin, sweet vermouth, and dill pickle juice. Upon serving the drink, Sheidlower explains it is a historic predecessor to the modern martini. (In general, he is an encyclopedia of sorts. When he serves our second cocktail, named the “Knights Who Say ‘Ni!’”—mezcal, ginger liqueur, and blackberry shrub—he has a detailed history of cocktail shrubs at the ready.)

Since the Tollbooth opened about six months ago (and began allowing press coverage in late October), Sheidlower has fielded his fair share of questions from guests. “People are curious about various aspects of the place,” he says. “They’re curious about the experience of other customers, they’re curious about the cocktails. Occasionally, there are some people who come because they think it’s going to be fun, irrespective of what we’re serving. But if they don’t care at all about cocktails, they’re probably in the wrong place."

Austin and Sheidlower both emphasize that the Tollbooth is a bar and not a theatrical experience. Yet its interior is expertly curated and feels almost like the set of a Hitchcock film. Most things double as practical and aesthetically pleasing, if eccentric: 100-year-old teacups; 70-year-old milk jugs scavenged from Dead Horse Bay in Brooklyn; a glass that Austin received from his grandmother; cocktail manuals; works from Susan Sontag and Argentine writer Jorge Luis Borges; the Bible. On a shelf of small bottles, the silver-haired, tuxedo-clad Dale DeGroff surveys my friend and me from the label of his aromatic pimento bitters.

There are also six hatch-marks carved into the wall directly to my left. With a small smirk, Sheidlower explains they signify something that happens very rarely during service. “When that thing happens,” he says, “we have a special knife that those who are responsible for this thing happening get to carve another hatch mark into the wall. Some people get extremely exercised about that—they try to guess what it is, or provoke it, or get me to tell. One guest even disrobed, thinking that, perhaps, that was the explanation. She did not get the luxury of adding herself to the wall."

If not for the dim lighting (and a strict no-photo policy), the Tollbooth would be an Instagram enthusiast’s paradise. But the quarters are so close, and the sights and tastes are so strangely satisfying, that the impulse to even glance at your smartphone falls by the wayside—an anomaly even in the world’s most top-shelf bars, and a testament to the Tollbooth as an all-around experience.

Shortly before leaving—my friend and I have just cleansed our palates by licking a small drop of 138-proof “Elixir Vegetal,” made by monks from the Grande Chartreuse monastery in France, off the backs of our hands—I notice a dark glass bottle perched atop the bar’s highest shelf. The phrase scrawled across the front reads: Leave Until Desperate. “[The bottle] is something that you really don’t want to go near,” Sheidlower says, and then reassures me, “It’s not poisonous. It’s not dangerous. We were making a mix [of alcohols], trying to come up with something interesting that we could use. And it was absolutely, without question, a total disaster. Like, ‘Okay, we’re going to throw this out.’ But then we were like, ‘You know what’”—he finishes with a wry laugh—“‘This is a memento of our arrogance.’"

The Threesome Tollbooth releases its next batch of reservations on November 13 at 1 p.m. EST. From $100 to $120 per person; threesometollbooth.com.